Searching for life's perfect fit.

Searching for Love After a Thirty-Year Hiatus

My reluctant plunge into online dating in my 50s

I met my husband at 16. We were married when I was 25. I was widowed three days before my 44th birthday.

Our two sons were in their early teens when we lost their father. He had been ill for quite some time, but the way he eventually passed away was sudden and traumatic. PTSD complicated our grief. I threw myself into tending to my boys, work and volunteering. Once they graduated, I created a this blog to finally process the sadness I had suppressed for years. My mind was too preoccupied and my spirit too full of heartache to allow time for dating.

And so, I waited nearly a decade to reenter the dating world. If you do the math, this seemed to be a pattern with me. What can I say? I needed to be REALLY sure before I truly committed.

Single and out of date

My husband was my first kiss, my first love, my first everything. My friend used to tease me that I had the dating skills of an adolescent: awkward, unsure and pretty much clueless. I had no playbook – no references to what I liked or disliked in a relationship. Flirtation was a skill that had dissipated long ago. Now in my fifties, I was about to enter foreign territory without comprehending the language or rules of the domain.

Back in high school, my biggest concerns were whether my side ponytail was attractively askew and the horror of my butt cheeks protruding beneath my Dolfin shorts. I could never have fathomed that a bodacious bootie would be considered alluring in the 21st century. I only wish a muffin top wasn’t an unwelcome collaborator in my middle-aged physique.

Looking for a Match made in OKCupid & other digital heavens

I had been pondering dating for a couple years before I resolved to be proactive. It was my hope that someone in my circle of friends would introduce me to a “nice guy” they knew. He would be properly vetted as engaging, financially secure and safe. There was one enormous snag in this scenario: Most of my friends were married. I was the only unattached mare in the posse. No stallions for miles.

And so, I reluctantly thrust myself into the realm of online dating. I honed my relationship seeking resume (aka profile) to the best of my novice ability. Dating Objectives, Activities & Interests and Bio were all crafted with a touch of wit and hidden desperation. Previous Experience was glaringly absent. I appraised pictures of myself until I found the few that I hoped portrayed subtle sexiness while concealing my double chin. Filled with apprehension, I shuddered as I posted it.

The responses began flooding in almost immediately. This is not to say I’m any more eye-catching than the previous gal to swipe across their screen – far from it. But if you’re female, new on the dating auction block and assumedly breathing, you’re a hot commodity.

Never in my wildest imagination could I have ever envisioned the types of characters soon parading through my account. There was an inordinate amount of men donning bizarre hairstyles including mullets and a Flock of Seagulls triple mohawk. I’d somewhat expected the gentlemen who obviously were lying about their age, but many were clearly decrepit. One even used a photo of himself in a hospital bed as his profile pic. Another chap sported a neck brace and still another proudly presented only his elbow scab. WTF? Did was he seeking someone to kiss his boo boo?

Call me sheltered, but I had never been propositioned to join a threesome, let alone on a daily basis. The erotic mischief requested included a “submissive guy seeking his dominant queen” who pledged to be castrated for his future mistress. There was the married fella searching for an addition to his polyamorous relationship. Only semi-good-looking gals need to respond as his wife “was quite homely” and abundantly jealous.

Then there were the usernames: AwesummaCumLaude, Eatyourkitty and Chocolate Reggie whose self-summary proclaimed, “Just a funny man with a big dick and full wallet,” were a few highlights of this brigade.

I came to the realization that I needed to apply some filters to sift through the invitations infiltrating my inbox and “likes” tallies. There were the simple sorts regarding age, height and marital status. Long distance romancers and professed CIA operatives were weeded out. Then there was the Not a Chance in Hells:

Grand displays of hunting and gathering prowess. Apparently, a lot of women are enticed by all sorts of aquatic life dangling from hooks. I had better fish to fry.

Costumes of any kind. Save your pirate garb for Halloween.

The inability to compose a simple sentence. I was a sucker for well-written note demonstrating they had actually read my profile. Terse missives such as “Hey Baby,” “Yummy,” and “Mmmm,” did not set this essayist’s heart aflutter.

A sprawling list of dislikes. Profiles spewing negativity and demands of “no drama” signaled someone who was seeking compliance, not a relationship.

Getting with the dating program

The laws of attraction are a bit cockeyed in the virtual world. You are introduced as the result of a succinct CV processed through an arbitrary algorithm. Physical mannerisms, nonverbal cues or pheromones are not in play just yet. Charm and other nuances are compressed like dough through a pasta machine, then transmitted via an LED display. This two-dimensional showmanship was superficial at its best. Counterfeit at its worst. It took me a while to acclimate and learn how to decipher these exhibitions. I’m not sure if I ever actually did.

With the simple click of a button, your interest in someone is proclaimed to the technological universe. Hopefully, they “wink” or like you back and the initial courtship begins. Last time I was in the dating arena, you danced with one partner at a time. When utilizing an app, one engages multiple prospective mates simultaneously. No more waiting to get home to check the answering machine. Messages appeared at all hours of the day and night. On some days, the frequent alerts buzzed my phone like a bumble bee stuck in a window shade. The cacophony of it all left me woozy. I soon became addicted to the rush of electronic seduction. On other days – many many days – the notifications fell silent. I checked and rechecked my phone, desperately seeking my fix.

“All that is gold does not glitter” – Tolkien

During this period, I relied heavily upon a close single friend for guidance. She was my Obi Wan – gifted in the ways of dating and an excellent counselor. Her eager apprentice, I regularly divulged the ups and downs of this unfamiliar terrain. We regaled each other with tales of fleeting passion, being ghosted and assorted profile oddities.

She recognized my dating immaturity, gradually teaching me to trust my own instincts and realize my self-worth. Each time I would come to her sorrowful from a rejection or breakup, she would always bestow the same advice, “I’m so sorry you’re in pain, but every relationship provides a valuable lesson. Whether it identified a trait in a man you can’t abide or gained an awareness of what brings you happiness, you have gleaned an insight into what you want out of a relationship.” Her mentorship proved invaluable.

This is not meant to be a manifesto railing about the perils of online dating. I know quite a few people who have successfully found their soulmates and/or future spouse. Personally, I frequently connected with men I found attractive, had a decently active dating life and various brief relationships. Did I find the next love of my life? That story is yet to be told…

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2 thoughts on “Searching for Love After a Thirty-Year Hiatus”

Oh Lisa! Hysterical. After John died I found myself lost! Drowning! No life preserver in the form of my husband. Just me!

And with Just Me, my friends decided I needed to find someone who might be a good match. Never mind that my perfect match was John, and his new zip code was heaven (with Matt and many many others).

I had not dated in 27 years. Fear was all I could feel. How does someone sell themselves? How does a woman look through a catalog like it’s the new Victoria’s Secret catalog?

Long story short-I found a genuine man! 65, retired, rancher in Leadville, CO. And here we are in Galveston, TX, quarantine delirious. Dennis is a keeper. He will never replace John, but he is helping me finish my dance card.

I wish you the same luck! I have to believe that Matt is beside you as the choices are made on the next gentleman in your life.

I’ve been dating a guy for just over a year. (Our anniversary was spent isolated from one another – Romantic trip to Paso postponed ) We didn’t meet online. Thinking of writing a piece about that, but we will see.

I, too, had so many reservations. Was not overly interested in Cliff at first – no immediate electricity – but I could never find a good reason to break it off with him and so I stayed. Began to realize he truly is the kindest man I have ever known, but so different than Matt in a lot of ways. It dawned on me that I was trying to find a Matt 2.0 and wasn’t open to other possibilities. Of course this was unfair to Cliff and limiting me. Once I got over that hurdle, the sparks began to fly.

Lisa Gastaldo

Lisa Gastaldo is a writer and marketing professional based in California. Her essays, which have covered everything from raising her two sons, losing her husband to cancer and battling it herself, as well as memories of life growing up a Valley Girl in the suburbs of LA, have appeared on Medium.com, The Good Men Project, and the Huffington Post. You can keep up with her on Twitter @ciaoluvlisa.

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